EP0884338B1 - Procede pour la production de mousse de polyurethane elastique - Google Patents
Procede pour la production de mousse de polyurethane elastique Download PDFInfo
- Publication number
- EP0884338B1 EP0884338B1 EP98110193A EP98110193A EP0884338B1 EP 0884338 B1 EP0884338 B1 EP 0884338B1 EP 98110193 A EP98110193 A EP 98110193A EP 98110193 A EP98110193 A EP 98110193A EP 0884338 B1 EP0884338 B1 EP 0884338B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- process according
- polyol
- weight
- functionality
- diisopropanolamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 7
- 239000011496 polyurethane foam Substances 0.000 title claims description 7
- 229920005862 polyol Polymers 0.000 claims abstract description 46
- 150000003077 polyols Chemical class 0.000 claims abstract description 45
- 239000000945 filler Substances 0.000 claims abstract description 19
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 18
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 239000003381 stabilizer Substances 0.000 claims abstract description 6
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 5
- 239000000654 additive Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920002396 Polyurea Polymers 0.000 claims abstract description 3
- 239000012190 activator Substances 0.000 claims abstract description 3
- 241001425800 Pipa Species 0.000 claims abstract 2
- 239000007858 starting material Substances 0.000 claims description 11
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 10
- 229940043276 diisopropanolamine Drugs 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 150000005828 hydrofluoroalkanes Chemical class 0.000 claims description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 229920005903 polyol mixture Polymers 0.000 claims 1
- 239000006260 foam Substances 0.000 abstract description 15
- 239000004971 Cross linker Substances 0.000 abstract description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004814 polyurethane Substances 0.000 abstract description 3
- 229920002635 polyurethane Polymers 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000007906 compression Methods 0.000 description 19
- 230000006835 compression Effects 0.000 description 17
- 230000032683 aging Effects 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- -1 2-hydroxyethoxyethyl Chemical group 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 229920001821 foam rubber Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000004872 foam stabilizing agent Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- GBAXGHVGQJHFQL-UHFFFAOYSA-N 1-(2-hydroxyethylamino)propan-2-ol Chemical compound CC(O)CNCCO GBAXGHVGQJHFQL-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- AXFVIWBTKYFOCY-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbutane-1,3-diamine Chemical compound CN(C)C(C)CCN(C)C AXFVIWBTKYFOCY-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- FZQMJOOSLXFQSU-UHFFFAOYSA-N 3-[3,5-bis[3-(dimethylamino)propyl]-1,3,5-triazinan-1-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN1CN(CCCN(C)C)CN(CCCN(C)C)C1 FZQMJOOSLXFQSU-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- TXOFSCODFRHERQ-UHFFFAOYSA-N N,N-Dimethylphenethylamine Chemical compound CN(C)CCC1=CC=CC=C1 TXOFSCODFRHERQ-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RGAMPJYGTCSRAG-UHFFFAOYSA-N bis[2-(diethylamino)ethyl] hexanedioate Chemical compound CCN(CC)CCOC(=O)CCCCC(=O)OCCN(CC)CC RGAMPJYGTCSRAG-UHFFFAOYSA-N 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000010097 foam moulding Methods 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N iso-pentane Natural products CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- XFLSMWXCZBIXLV-UHFFFAOYSA-N n,n-dimethyl-2-(4-methylpiperazin-1-yl)ethanamine Chemical compound CN(C)CCN1CCN(C)CC1 XFLSMWXCZBIXLV-UHFFFAOYSA-N 0.000 description 1
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical class [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6552—Compounds of group C08G18/63
- C08G18/6558—Compounds of group C08G18/63 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/657—Compounds of group C08G18/63 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of C08G18/3225 or C08G18/3271 or polyamines of C08G18/38
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4072—Mixtures of compounds of group C08G18/63 with other macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/005—< 50kg/m3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S521/914—Polyurethane cellular product formed from a polyol which has been derived from at least two 1,2 epoxides as reactants
Definitions
- the invention relates to a method for producing elastic Flexible polyurethane foams.
- two large product groups are used as soft, elastic, cellular upholstery materials. These are on the one hand the soft elastic polyurethanes and on the other hand the latex foams. There are differences between the two product groups in the starting products, the manufacturing process and the mechanical properties as well as their application.
- latex foams there is a slightly different course of the compression hardness curve according to DIN 53577 and ISO 3386, parts 1 and 2.
- polyurethane foams latex foams do not show a pronounced compression hardness plateau, but rather an almost linear increase in compression hardness in a certain compression range. For certain applications, this characteristic is desirable or even fixed.
- the average bulk density of the latex foams is at least 60 kg / m 3 or mostly higher and this has compression hardness between 3 and 4.5 kPa.
- Such types of foam are preferably used to manufacture high quality mattresses.
- Polyurethane foams usually show higher in this bulk density range Compression hardness and also another compression hardness / compression process.
- these foams are said to have low permanent values Deformation as well as low values after wet aging. This is a particularly important criterion.
- blowing agents such as hydrofluoroalkanes or alkenes such as Pentane, i-pentane, cyclopentane or carbon dioxide are used become.
- the filler content, based on the polyol component B) from i) and ii), is 2 to 30, preferably 3 to 15, particularly preferably 3 to 10% filler PHD, SAN or PIPA. Since the filler dispersions ii) generally between 10 and 40% filler manufactured, this must be taken into account accordingly.
- A is often used Filler content of 20%, so that e.g. at 25 parts by weight ii) and 75 parts by weight i) a filler content of 5% by weight, based on the polyol component B) becomes.
- Starting materials on the side of the polyols i) are polyols which are obtained by addition of Alkylene oxides such as ethylene oxide and propylene oxide to higher functional starters such as Sorbitol, mannitol or sucrose alone or in combination with starters such as ethylene glycol, Propylene glycol, glycerin, trimethylolpropane or pentaerythritol, so that functionality between 4 and 8 can be set.
- Alkylene oxides such as ethylene oxide and propylene oxide
- higher functional starters such as Sorbitol, mannitol or sucrose alone or in combination with starters such as ethylene glycol, Propylene glycol, glycerin, trimethylolpropane or pentaerythritol, so that functionality between 4 and 8 can be set.
- Starters for the filler polyols ii) are glycerol, trimethylolpropane, pentaerythritol, Propylene glycol and ethylene glycol.
- Alkanolamine crosslinkers G include compounds such as diisopropanolamine, triisopropanolamine, Triethanolamine, diethanolamine, 2-hydroxyethyl-2-hydroxypropylamine and bis- (2-hydroxyethoxyethyl) amine or mixtures thereof.
- unmodified polyisocyanates e.g. the 2,4- and 2,6-tolylene diisocyanate as well as any mixtures of these isomers (“TDI”), polyphenylpolymethylene polyisocyanates, as by aniline-formaldehyde condensation and subsequent phosgenation are produced (“raw MDI").
- Particularly stabilizers F) are polyether siloxanes, preferably water-insoluble ones Representative, in question. These connections are generally structured that a short-chain copolymer of ethylene oxide and propylene oxide with a polydimethylsiloxane residue is connected. Such foam stabilizers are e.g. in U.S. Patents 2,834,748, 2,917,480 and 3,629,308 and U.S. Patent 2,917,480 described.
- Catalysts F of the type known per se are e.g. tertiary amines, such as triethylamine, Tributylamine, N-methylmorpholine, N-ethylmorpholine, N, N, N ', N'-tetramethylethylene diamine, Pentamethyl-diethylenetriamine and higher homologues (DE-A 2 624 527 and 2 624 528), 1,4-diazabicyclo- (2,2,2) -octane, N-methyl-N'dimethylaminoethylpiperazine, Bis (dimethylaminoalkyl) piperazines, N, N-dimethylbenzylamine, N, N-dimethylcyclohexylamine, N, N-diethylbenzylamine, bis (N, N-diethylaminoethyl) adipate, N, N, N ', N'-tetramethyl-1,3-butanediamine,
- Organic metal compounds in particular, can also be used as catalysts F) organic tin compounds can be used.
- organic tin compounds come in addition to sulfur-containing compounds such as di-n-octyl tin mercaptide preferably tin (II) salts of carboxylic acids such as tin (II) acetate, tin (II) octoate, Tin (II) ethylhexoate and tin (II) laurate and the tin (IV) compounds, e.g. dibutyl tin oxide, Dibutyltin dichloride, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate or dioctyltin diacetate.
- sulfur-containing compounds such as di-n-octyl tin mercaptide preferably tin (II) salts of carboxylic acids such as tin (II) a
- Components F further additives and foam stabilizers and cell regulators, Reaction retarders, stabilizers, flame retardants, plasticizers, Dyes and fillers as well as fungistatic and bactereostatic effective substances as well as details on use and mode of action these additives are published in the Plastics Manual, Volume VII Vieweg and Höchtlen, Carl Hanser Verlag, Kunststoff 1993, 3rd edition, e.g. on pages 104 to 127.
- the reaction components are prepared according to that known per se One-step process, the prepolymer process or the semi-prepolymer process implemented, often using machinery, e.g. those described in US Pat. No. 2,764,565. Details about Processing devices that are also suitable according to the invention in the plastic manual, volume VII, edited by Vieweg and Höchtlen, Carl-Hanser-Verlag, Kunststoff 1966, e.g. described on pages 121 to 205.
- the implementation is usually carried out in a range from 90 to 130.
- foaming can also be carried out in foam production closed forms.
- the reaction mixture is in entered a form.
- Metal e.g. Aluminum
- Plastic e.g. Epoxy resin
- the foamable reaction mixture foams in the mold and forms the Moldings.
- the foam molding can be carried out so that the Has molded part on its surface cell structure. But it can also be done this way be that the molded part has a compact skin and a cellular core receives. According to the invention, one can proceed in this connection in such a way that one enters so much foamable reaction mixture in the mold that the formed Foam fills the shape straight.
- the foams are preferably produced by block foaming.
- Polyether polyol of OH number 28 prepared by adding 82% by weight of propylene oxide and 18 wt .-% ethylene oxide on sorbitol as a starter with predominantly primary OH terminal groups
- the polyol i) according to the invention is replaced by a polyol having an OH number of 28 82% by weight of propylene oxide and 18% by weight of ethylene oxide, but with trimethylolpropane as a starter and predominantly primary OH end groups, you get an unstable Raw material mixture that cannot be foamed in this context.
- Examples 4 and 5 are produced with a compression hardness of 3.4 or 2.8 KPa with a filler content of 20 or 10% by weight and a bulk density of 30 kg / m 3 on the basis of trifunctional polyols and alkanolamine crosslinking with diethanolamine , result in wet aging values that are between 12 and 15%.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Claims (11)
- Procédé de fabrication d'une mousse de polyuréthane souple et élastique par transformation deA) polyisocyanates ou de prépolymères de polyisocyanate,B) composés, d'un poids moléculaire de 500 à 18 000, avec au moins deux atomes d'hydrogène pouvant réagir avec des isocyanates contenanti) au moins un polyétherpolyol de fonctionnalité 4 à 8, etii) au moins un polyol contenant une charge sélectionné parmi le groupement des types de polyol de fonctionnalité 2,5 à 4 modifiés par du PHD, SAN ou PIPA,C) le cas échéant d'autres composés, d'un poids moléculaire de 32 à 499, avec au moins deux atomes d'hydrogène pouvant réagir avec des isocyanates,D) l'eau,E) le cas échéant des agents moussants,F) des activateurs, des stabilisants ainsi que d'autres additifs connus en soi,
ainsi queG) diisopropanolamine ou un mélange de diisopropanolamine et de triéthanolamine comme agent de réticulation alcanolamine. - Procédé selon la revendication 1, caractérisé en ce qu'on utilise un composant polyol i) avec une fonctionnalité d'amorceur de 4 à 8 et un poids équivalent de 100 à 4 000 et ii) des dispersions de polyurée.
- Procédé selon la revendication 1, caractérisé en ce qu'on utilise un composant polyol i) avec une fonctionnalité d'amorceur de 4 à 8, et un poids équivalent de 100 à 4 000 et ii) des dispersions de SAN.
- Procédé selon la revendication 1, caractérisé en ce qu'on utilise un composant polyol i) avec une fonctionnalité d'amorceur de 4 à 8 et un poids équivalent de 100 à 4 000 et ii) des dispersions de PIPA.
- Procédé selon les revendications 1 à 4, caractérisé en ce que le composant réactif B) est composé de 60 à 90 parties en poids de i) et 10 à 40 parties en poids de ii), la proportion de charge dans le mélange polyol constitué de i) et ii) étant de 2 à 30 parties en poids, sur base du composant B).
- Procédé selon les revendications 1 à 5, caractérisé en ce que le composant polyol i) présente des groupements terminaux OH principalement primaires et une teneur en oxyde d'éthylène de 10 à 30% en poids, ainsi qu'un poids équivalent de 100 à 4 000.
- Procédé selon les revendications 1 à 6, caractérisé en ce qu'on utilise comme agent de réticulation alcanolamine G) de la diisopropanolamine.
- Procédé selon les revendications 1 à 6, caractérisé en ce qu'on utilise comme agent de réticulation alcanolamine G) un mélange constitué de triéthanolamine et de diisopropanolamine.
- Procédé selon l'une des revendications 1 à 8, caractérisé en ce qu'on utilise comme polyisocyanate du diisocyanate de toluylène.
- Procédé selon l'une des revendications 1 à 8, caractérisé en ce qu'on utilise comme polyisocyanates ou prépolymères de polyisocyanate, du diisocyanate de diphénylméthane ou du diisocyanate de toluylène le cas échéant modifié par des groupements uréthane, urée, biuret, allophanate, carbodiimide ou uretdione ou leurs prépolymères ainsi que leurs mélanges.
- Procédé selon l'une des revendications 1 à 10, caractérisé en ce qu'on utilise comme agent moussant du dioxyde de carbone, des hydrofluoroalcanes et/ou des alcanes avec 4 à 5 atomes de carbone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI9830147T SI0884338T1 (en) | 1997-06-13 | 1998-06-04 | Process for production of high resilient polyurethane foam |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19725020A DE19725020C2 (de) | 1997-06-13 | 1997-06-13 | Verfahren zur Herstellung elastischer Polyurethanweichschaumstoffe |
| DE19725020 | 1997-06-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0884338A1 EP0884338A1 (fr) | 1998-12-16 |
| EP0884338B1 true EP0884338B1 (fr) | 2002-10-02 |
Family
ID=7832386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP98110193A Expired - Lifetime EP0884338B1 (fr) | 1997-06-13 | 1998-06-04 | Procede pour la production de mousse de polyurethane elastique |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5977198A (fr) |
| EP (1) | EP0884338B1 (fr) |
| AT (1) | ATE225376T1 (fr) |
| CA (1) | CA2240225C (fr) |
| DE (2) | DE19725020C2 (fr) |
| DK (1) | DK0884338T3 (fr) |
| ES (1) | ES2184170T3 (fr) |
| NO (1) | NO318665B1 (fr) |
| PL (1) | PL192484B1 (fr) |
| PT (1) | PT884338E (fr) |
| SI (1) | SI0884338T1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6586501B1 (en) | 1999-01-20 | 2003-07-01 | Cabot Corporation | Aggregates having attached polymer groups and polymer foams |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2374415A1 (fr) * | 1999-05-31 | 2000-12-07 | Dirk Rene Leonie Ramael | Polyols modifies par un polymere et leur utilisation pour la fabrication d'articles en polyurethane |
| KR100490004B1 (ko) * | 1999-12-17 | 2005-05-17 | 카오카부시키가이샤 | 폴리우레탄의 제조법 |
| DE19962911C2 (de) | 1999-12-23 | 2002-11-21 | Bayer Ag | Flammwidriger HR-Kaltformschaum mit reduzierter Rauchgasintensität und -toxizität |
| JP2003520873A (ja) | 2000-01-17 | 2003-07-08 | ハンツマン・インターナショナル・エルエルシー | フリーライズまたはスラブストック軟質ポリウレタンフォームの製造方法 |
| DE10110553A1 (de) * | 2001-03-05 | 2002-09-12 | Basf Ag | Verfahren zur Herstellung von Polyurethan-Weichschaumstoffen |
| DE10129062A1 (de) * | 2001-06-15 | 2002-12-19 | Basf Ag | Verfahren zur Herstellung von hochelastischen Polyurethanschaumstoffen |
| EP1447419A1 (fr) * | 2003-02-11 | 2004-08-18 | Shell Internationale Researchmaatschappij B.V. | Utilisation d'une formulation de polyols |
| PL364942A1 (en) * | 2003-02-11 | 2004-08-23 | Shell Internationale Research Maatschappij B.V. | Application of polyol compound and method for manufacturing foam |
| DE102004060800A1 (de) * | 2004-12-17 | 2007-05-03 | Bayer Materialscience Ag | Kunststoffformteile aus gegebenenfalls gefüllten Polyurethanen und deren Verwendung |
| US20070225393A1 (en) * | 2006-03-27 | 2007-09-27 | Arnold Allen R Jr | Crosslinkers for minimizing deterioration of polyurethane foams |
| DE102006030531A1 (de) * | 2006-07-01 | 2008-01-03 | Goldschmidt Gmbh | Siliconstabilisatoren für flammgeschützte Polyurethan- bzw. Polyisocyanurat-Hartschaumstoffe |
| US8552078B2 (en) | 2006-10-17 | 2013-10-08 | Air Products And Chemicals, Inc. | Crosslinkers for improving stability of polyurethane foams |
| DE102006060376A1 (de) * | 2006-12-20 | 2008-06-26 | Bayer Materialscience Ag | Verfahren zur Herstellung von PIPA-Polyolen zur Herstellung von hochelastischen Polyurethan-Weichschaumstoffen |
| JP4691683B2 (ja) * | 2009-06-02 | 2011-06-01 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | ポリウレタン発泡組成物およびポリウレタンフォームの製造方法 |
| ES2404734B2 (es) * | 2011-10-05 | 2014-01-29 | Centro Tecnológico De Grupo Copo, S.L.U. | Composición química para obtención de poliuretano. |
| BR112016005362B1 (pt) * | 2013-09-13 | 2021-03-09 | Dow Global Technologies Llc | método de produção de uma espuma viscoelástica |
| EP3898745B1 (fr) * | 2018-12-19 | 2023-08-30 | Basf Se | Mousse souple en polyuréthane aux propriétés d'utilisation continue améliorées |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR704224A (fr) * | 1929-12-19 | 1931-05-15 | Siemens Ag | Procédé pour la compensation électrique de câbles sous-marins |
| FR1056520A (fr) * | 1952-05-14 | 1954-03-01 | Exxon Standard Sa | Procédé de fabrication d'émulsifiants pour liants hydrocarbones et produits en résultant |
| NO176611C (no) * | 1988-07-12 | 1995-05-03 | Arco Chem Tech | Polymerpolyol nyttig ved fremstillingen av fleksible polyuretanskum og dens anvendelse |
| GB9126740D0 (en) * | 1991-12-17 | 1992-02-12 | Ici Plc | Polyol compositions |
| GB9126741D0 (en) * | 1991-12-17 | 1992-02-12 | Ici Plc | Polyurethane foams |
| US6521674B1 (en) * | 1993-10-01 | 2003-02-18 | Carpenter Co. | Latex-like flexible polyurethane foam and process for making same |
| DE19508079A1 (de) * | 1995-03-08 | 1996-09-12 | Bayer Ag | Verfahren zur Herstellung von hochelastischen Polyurethanschaumstoffen |
| CZ351996A3 (en) * | 1995-12-07 | 1997-06-11 | Shell Int Research | Polyol formulation for preparing flexible polyurethane foam similar to latex |
-
1997
- 1997-06-13 DE DE19725020A patent/DE19725020C2/de not_active Expired - Fee Related
-
1998
- 1998-06-04 ES ES98110193T patent/ES2184170T3/es not_active Expired - Lifetime
- 1998-06-04 EP EP98110193A patent/EP0884338B1/fr not_active Expired - Lifetime
- 1998-06-04 PT PT98110193T patent/PT884338E/pt unknown
- 1998-06-04 SI SI9830147T patent/SI0884338T1/xx unknown
- 1998-06-04 DE DE59805758T patent/DE59805758D1/de not_active Expired - Lifetime
- 1998-06-04 DK DK98110193T patent/DK0884338T3/da active
- 1998-06-04 AT AT98110193T patent/ATE225376T1/de active
- 1998-06-10 CA CA002240225A patent/CA2240225C/fr not_active Expired - Fee Related
- 1998-06-10 PL PL326779A patent/PL192484B1/pl unknown
- 1998-06-11 NO NO19982683A patent/NO318665B1/no unknown
- 1998-06-12 US US09/097,313 patent/US5977198A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6586501B1 (en) | 1999-01-20 | 2003-07-01 | Cabot Corporation | Aggregates having attached polymer groups and polymer foams |
Also Published As
| Publication number | Publication date |
|---|---|
| NO982683D0 (no) | 1998-06-11 |
| DE19725020A1 (de) | 1998-12-24 |
| NO982683L (no) | 1998-12-14 |
| DE59805758D1 (de) | 2002-11-07 |
| PL192484B1 (pl) | 2006-10-31 |
| US5977198A (en) | 1999-11-02 |
| DK0884338T3 (da) | 2003-02-03 |
| DE19725020C2 (de) | 2001-10-31 |
| ES2184170T3 (es) | 2003-04-01 |
| PT884338E (pt) | 2002-12-31 |
| EP0884338A1 (fr) | 1998-12-16 |
| PL326779A1 (en) | 1998-12-21 |
| ATE225376T1 (de) | 2002-10-15 |
| CA2240225C (fr) | 2007-09-18 |
| SI0884338T1 (en) | 2002-12-31 |
| CA2240225A1 (fr) | 1998-12-13 |
| NO318665B1 (no) | 2005-04-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0884338B1 (fr) | Procede pour la production de mousse de polyurethane elastique | |
| EP0331941B1 (fr) | Procédé de préparation de mousses de polyuréthane flexibles, durcissant à froid et ayant d'excellentes propriétés d'assourdissement | |
| EP0296449B1 (fr) | Procédé de préparation de mousses souples de polyuréthanes durcissables à froid | |
| EP0991686B1 (fr) | Procede de production de mousses rigides de polyurethanne a alveoles fermees a faible conductibilite thermique | |
| EP0845485B1 (fr) | Mousses de polyuréthane souples et élastiques et leur procédé de préparation | |
| EP0805831B1 (fr) | Utilisation de polyols en base de toluenediamine oxide de propylene dans mousses de polyurethane rigides | |
| EP1935912B1 (fr) | Procédé destiné à la fabrication de polyols PIPA destinés à la fabrication de mousses souples de polyuréthane hautement élastiques | |
| EP0555721A1 (fr) | Procédé de préparation de mousses de polyuréthane flexibles durcissant à froid | |
| DE2624528A1 (de) | Verfahren zur herstellung von polyurethanschaumstoffen | |
| EP1473313B1 (fr) | Pieces moulees flexibles preparees à partir de polyurethane souffle à l'azote, l'air ou au dioxyde de carbone et leur utilisation | |
| EP1650240B1 (fr) | Mousse flexible de polyurethane ayant une faible densité et à résistance réduite à la compression | |
| DE69801421T2 (de) | Isocyanatzusammensetzungen zur herstellung von polyurethanschaumstoffen mit geringer dichte | |
| DE2937330A1 (de) | Verfahren zur herstellung von elastischen, flammkaschierbaren und hochfrequenzverschweissbaren polyurethanschaumstoffen | |
| EP0826706A2 (fr) | Compositions moussantes de polyuréthane ayant un bon comportement rhéologique et procédé de préparation d'objets moulès à base de mousses polyuréthanes | |
| CH636364A5 (en) | Process for the preparation of cold-curing, flexible foams containing urethane groups | |
| EP0731120B1 (fr) | Procédé de préparation de mousses de polyuréthane à grande élasticité | |
| EP0379008B1 (fr) | Procédé de préparation de mousses de polyuréthane moulées souples à basse masse volumique apparente | |
| EP0472080A2 (fr) | Procédé de préparation de mousses rigides de polyuréthane | |
| DE3910102C1 (fr) | ||
| EP0352528A2 (fr) | Procédé de préparation de mousses de polyuréthane | |
| DE2444331A1 (de) | Verfahren zur herstellung von superelastischen polyurethanschaumstoffen (kaltschaumstoffen) | |
| DE2431968A1 (de) | Verfahren zur herstellung von schaumstoffen | |
| DE2717653A1 (de) | Verfahren zur herstellung von kalthaertenden, flexiblen, urethangruppen aufweisenden schaumstoffen | |
| DD297420A5 (de) | Verfahren zur herstellung von polyurethan-weichformschaumstoffen niedriger rohdichte | |
| DE2502658A1 (de) | Verfahren zur herstellung von kalthaertenden, urethangruppen aufweisenden schaumstoffen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LI NL PT SE |
|
| AX | Request for extension of the european patent |
Free format text: AL;LT;LV;MK;RO;SI |
|
| 17P | Request for examination filed |
Effective date: 19990616 |
|
| AKX | Designation fees paid |
Free format text: AT BE CH DE DK ES FI FR GB GR IE IT LI NL PT SE |
|
| AXX | Extension fees paid |
Free format text: SI PAYMENT 19990616 |
|
| 17Q | First examination report despatched |
Effective date: 20001207 |
|
| GRAG | Despatch of communication of intention to grant |
Free format text: ORIGINAL CODE: EPIDOS AGRA |
|
| GRAG | Despatch of communication of intention to grant |
Free format text: ORIGINAL CODE: EPIDOS AGRA |
|
| GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
| GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LI NL PT SE |
|
| AX | Request for extension of the european patent |
Free format text: SI PAYMENT 19990616 |
|
| REF | Corresponds to: |
Ref document number: 225376 Country of ref document: AT Date of ref document: 20021015 Kind code of ref document: T |
|
| REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D Free format text: NOT ENGLISH |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: NV Representative=s name: E. BLUM & CO. PATENTANWAELTE Ref country code: CH Ref legal event code: EP |
|
| GBT | Gb: translation of ep patent filed (gb section 77(6)(a)/1977) |
Effective date: 20021002 |
|
| REG | Reference to a national code |
Ref country code: IE Ref legal event code: FG4D Free format text: GERMAN |
|
| REF | Corresponds to: |
Ref document number: 59805758 Country of ref document: DE Date of ref document: 20021107 |
|
| REG | Reference to a national code |
Ref country code: PT Ref legal event code: SC4A Free format text: AVAILABILITY OF NATIONAL TRANSLATION Effective date: 20021030 |
|
| REG | Reference to a national code |
Ref country code: DK Ref legal event code: T3 |
|
| REG | Reference to a national code |
Ref country code: GR Ref legal event code: EP Ref document number: 20020404227 Country of ref document: GR |
|
| REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2184170 Country of ref document: ES Kind code of ref document: T3 |
|
| ET | Fr: translation filed | ||
| PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
| 26N | No opposition filed |
Effective date: 20030703 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GR Payment date: 20040518 Year of fee payment: 7 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: IE Payment date: 20040602 Year of fee payment: 7 |
|
| REG | Reference to a national code |
Ref country code: SI Ref legal event code: IF |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20050606 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20060103 |
|
| REG | Reference to a national code |
Ref country code: IE Ref legal event code: MM4A |
|
| REG | Reference to a national code |
Ref country code: SI Ref legal event code: KO00 Effective date: 20060331 |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: PFA Owner name: BAYER AG Free format text: BAYER AG# #51368 LEVERKUSEN (DE) -TRANSFER TO- BAYER AG# #51368 LEVERKUSEN (DE) |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DK Payment date: 20080612 Year of fee payment: 11 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FI Payment date: 20080613 Year of fee payment: 11 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20090604 |
|
| REG | Reference to a national code |
Ref country code: DK Ref legal event code: EBP |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DK Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20090630 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 20110614 Year of fee payment: 14 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 20120626 Year of fee payment: 15 |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20120630 Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20120630 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: SE Payment date: 20130612 Year of fee payment: 16 Ref country code: GB Payment date: 20130529 Year of fee payment: 16 |
|
| REG | Reference to a national code |
Ref country code: NL Ref legal event code: V1 Effective date: 20140101 |
|
| REG | Reference to a national code |
Ref country code: DE Ref legal event code: R081 Ref document number: 59805758 Country of ref document: DE Owner name: BAYER INTELLECTUAL PROPERTY GMBH, DE Free format text: FORMER OWNER: BAYER MATERIALSCIENCE AKTIENGESELLSCHAFT, 51373 LEVERKUSEN, DE Effective date: 20140317 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20140101 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20140605 |
|
| REG | Reference to a national code |
Ref country code: SE Ref legal event code: EUG |
|
| GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20140604 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20140604 |
|
| REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 18 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: ES Payment date: 20150527 Year of fee payment: 18 Ref country code: PT Payment date: 20150601 Year of fee payment: 18 Ref country code: DE Payment date: 20150527 Year of fee payment: 18 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20150608 Year of fee payment: 18 Ref country code: BE Payment date: 20150612 Year of fee payment: 18 Ref country code: AT Payment date: 20150527 Year of fee payment: 18 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: IT Payment date: 20150625 Year of fee payment: 18 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20160630 |
|
| REG | Reference to a national code |
Ref country code: DE Ref legal event code: R119 Ref document number: 59805758 Country of ref document: DE |
|
| REG | Reference to a national code |
Ref country code: AT Ref legal event code: MM01 Ref document number: 225376 Country of ref document: AT Kind code of ref document: T Effective date: 20160604 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: PT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20161205 |
|
| REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST Effective date: 20170228 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20160630 Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20170103 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: AT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20160604 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20160604 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: ES Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20160605 |
|
| REG | Reference to a national code |
Ref country code: ES Ref legal event code: FD2A Effective date: 20181119 |